--- title: "Chester Holidays 2026 from £731 | Expedia.co.uk" description: "Book your ATOL protected Chester holiday today! Enjoy flexibility with our interest-free instalments & book now pay later option. Fully refundable rates on most hotels." canonical: "https://www.expedia.co.uk/Chester.d183058.Holidays-City-Breaks" language: en-GB market: GB currency: GBP prices_as_of: 2026-11-14T04:18:28Z --- # Chester Holidays from £731 ![A calm river with boats, wooden docks, and buildings along the shore.](https://images.trvl-media.com/place/183058/f457b867-7f08-4489-b983-3426d68ada3d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £750 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Packages with flights are ATOL protected #### Your Chester Holiday The best way to experience this vibrant city is with a custom-made Chester holiday package. Stay in the neighbourhood of Essex Village, which is good for walking, hiking and views or choose someplace else — our packages are all about you. [Essex Steam Train](https://www.expedia.co.uk/Essex-Steam-Train-Essex.d6171206.Attraction), [Goodspeed Opera House](https://www.expedia.co.uk/Goodspeed-Opera-House-East-Haddam.d6089799.Attraction) and [Essex Island Marina](https://www.expedia.co.uk/Essex-Island-Marina-Essex.d6326375.Attraction) are just some of the many sights you'll want to check out during your trip to Chester. Check out Expedia's extensive range of travel options and begin planning your perfect holiday to Chester now. ## Top Chester flight + hotel deals Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A sign for Pier Blue Guesthouse surrounded by lush greenery and vibrant flowers.](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/b52d4aeb.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![Two beds with white linens and brown pillows, a bedside lamp, and a patterned throw blanket.](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/7a063086.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **24 Dec - 28 Dec** ### [Pier Blue Inn Old Saybrook - Essex + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-24/2026-12-28/?FromAirport=LHR&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12143&dealMarker=&paandie=true&cabinClass=e) Saybrook Manor 4 nights **8.0/10** \- Very good (1,000 reviews) Return • London (LHR) - New Haven (HVN) LHR - JFK • 1 stop LGA - LHR • 1 stop [~~£815~~](https://www.expedia.co.uk/) **£731** per traveller found 7 hours ago - ![A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/fc6ee41c.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/97b402fd.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **24 Dec - 28 Dec** ### [Water's Edge Resort & Spa + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-24/2026-12-28/?FromAirport=LHR&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=9679841&dealMarker=&paandie=true&cabinClass=e) Westbrook Center 4 nights **8.8/10** \- Excellent (1,010 reviews) "It was a lovely property and close to stores and places to eat." Reviewed November 13, 2026 Return • London (LHR) - New Haven (HVN) LHR - JFK • 1 stop LGA - LHR • 1 stop [~~£999~~](https://www.expedia.co.uk/) **£849** per traveller found 7 hours ago - ![A two-story house with a steeply pitched roof, green shutters, and a brick entrance.](https://images.trvl-media.com/lodging/113000000/112910000/112907700/112907611/66ba9518.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A swimming pool with lounge chairs and a white fence.](https://images.trvl-media.com/lodging/113000000/112910000/112907700/112907611/6a9a51fd.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **24 Dec - 28 Dec** ### [Head of Pond House + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-24/2026-12-28/?FromAirport=LHR&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=112907611&dealMarker=&paandie=true&cabinClass=e) Water Mill 4 nights **10/10** \- Exceptional (18 reviews) "Monika is a warm, energetic and helpful host at every turn while granting your privacy . The rooms were immaculate and beautifully designed with comfortable mattress, thick towels, lovely sheets, a reading chair with ottoman, good lighting , an antique sturdy writing desk. Thick bathrobes and a great bathroom along with excellent controls for setting AC or heat too. Breakfasts were delicious with juice, fresh fruit, homemade scones and muffins, pastries, and yogurt , granola, one morning,a..." Reviewed October 12, 2026 Return • London (LHR) - New Haven (HVN) LHR - JFK • 1 stop LGA - LHR • 1 stop [~~£1,103~~](https://www.expedia.co.uk/) **£1,047** per traveller found 7 hours ago ## Where to stay in Chester Find the best Chester areas for the activities you enjoy most. - [Chester Center](#) ![A plate of food with three square pieces topped with greens and caviar.](https://images.trvl-media.com/place/183058/132ef6d3-548e-4eca-851b-2f71fb5ffb6e.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by Annette Babek [View properties in map for Chester Center](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=553248635976479536) ### Chester Center If you're spending some time in Chester Center, Norma Terris Theater and Connecticut Valley Railroad State Park Trail are top sights worth seeing. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976479536) ## Discover the most popular places to visit in Chester ### Norma Terris Theater The Norma Terris Theatre is Goodspeed Musicals' developmental space where innovative productions debut. In this intimate setting, audiences witness tomorrow's Broadway hits evolve before their eyes. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665705) ## Chester Hotel Deals ### [Clinton Motel](https://www.expedia.co.uk/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f9bec315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 163 East Main Street, Clinton, CT, 06413, US - Location: 8.9 mi from Chester - Star rating: 2.5/5 - Guest rating: 8.6/10 (Excellent, 351 reviews) - Price: £68, includes taxes & fees, 15 Nov - 16 Nov ### [Quality Inn Old Saybrook - Westbrook](https://www.expedia.co.uk/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/a17cae6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 100 Essex Rd, Old Saybrook, CT, 06475, US - Location: 8.6 mi from Chester - Star rating: 2.5/5 - Guest rating: 7.8/10 (Good, 1000 reviews) - Price: £88, includes taxes & fees, 6 Dec - 7 Dec ### [Pier Blue Inn Old Saybrook - Essex](https://www.expedia.co.uk/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![A sign for Pier Blue Guesthouse surrounded by lush greenery and vibrant flowers.](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/b52d4aeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1430 Boston Post Rd, Old Saybrook, CT, 06475, US - Location: 8.9 mi from Chester - Star rating: 2/5 - Guest rating: 8/10 (Very good, 1000 reviews) - Price: £67, includes taxes & fees, 15 Nov - 16 Nov ### [Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy](https://www.expedia.co.uk/East-Haddam-Hotels-Postcard-Cabins-Machimoodus.h110235311.Hotel-Information) ![A cabin surrounded by a natural forest setting with a fire pit and picnic table.](https://images.trvl-media.com/lodging/111000000/110240000/110235400/110235311/b277a524.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 298 E Haddam Moodus Rd, East Haddam, CT, 06469, US - Location: 6.1 mi from Chester - Star rating: 2.5/5 - Guest rating: 9.4/10 (Exceptional, 223 reviews) - Price: £145, includes taxes & fees, 14 Dec - 15 Dec - Review: Everything was great just make sure you get there before it gets dark out. It’s relevantly hard to find the cabins in the pitch black. Overall the area was very quiet. We had neighbors but you really can’t hear anyone around you. It’s a great way to disconnect and unwind. ### [Water's Edge Resort & Spa](https://www.expedia.co.uk/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/fc6ee41c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1525 Boston Post Road, Westbrook, CT, 06498, US - Location: 8.7 mi from Chester - Star rating: 3.5/5 - Guest rating: 8.8/10 (Excellent, 1010 reviews) - Price: £129, includes taxes & fees, 23 Nov - 24 Nov - Review: It was a lovely property and close to stores and places to eat. ### [Motel 6 Old Saybrook, CT](https://www.expedia.co.uk/Old-Saybrook-Hotels-Super-8-By-Wyndham-Old-Saybrook.h855251.Hotel-Information) ![A hotel room with a bed, bedside tables, a desk, a chair, a television, and a painting on the wall.](https://images.trvl-media.com/lodging/1000000/860000/855300/855251/w2651h1980x111y0-13b1f665.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 37 Spencer Plain Rd, Old Saybrook, CT, 06475, US - Location: 8.5 mi from Chester - Star rating: 2/5 - Guest rating: 7/10 (Good, 956 reviews) - Price: £55, includes taxes & fees, 18 Nov - 19 Nov - Review: Shower was broken, holes in the walls, people banging on the walls at all times of morning/night, cleaning person was very dirty, people living in hotel as their residence. ### [Spark by Hilton Guilford](https://www.expedia.co.uk/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![A breakfast bar with various food items and a coffee machine.](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/dc9b088b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 300 Boston Post Rd, Guilford, CT, 06437, US - Location: 12.1 mi from Chester - Star rating: 2.5/5 - Guest rating: 9/10 (Wonderful, 236 reviews) - Price: £80, includes taxes & fees, 10 Dec - 11 Dec - Review: This was my first time staying and will absolutely be coming back! The rooms were clean and lovely. Breakfast was a perfect start to our early mornings. And the staff was so nice and welcoming! ### [Copper Beech Inn](https://www.expedia.co.uk/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information) ![A large, two-story house with a wrap-around porch and a conservatory.](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/a99c206a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 46 Main Street, Ivoryton, CT, 06442, US - Location: 4.6 mi from Chester - Star rating: 4/5 - Guest rating: 8.6/10 (Excellent, 530 reviews) - Price: £243, includes taxes & fees, 15 Nov - 16 Nov - Review: Nice stay. Quite, Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [See all properties in Chester](https://www.expedia.co.uk/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29®ionId=183058&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Frequently Asked Questions ### How much does a Chester travel package cost? Maybe less than you imagined — from a low £731, actually! By bundling flights, hotels and car rentals into a custom-built package, your trip to Chester is only clicks away. ### If I'm not able to travel, can I cancel my Chester travel package? You can. We totally understand that even the best-laid plans can fail, so we're here to help if you have to make changes to your Chester travel package. It may be possible to cancel or amend your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Head to our [Customer Service Portal](https://www.expedia.co.uk/service/?langid=1033) for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees. ### How do I get a cheap travel package to Chester? Combine your bookings with Expedia to save big on your next trip. With over 550 air carriers and 1,000,000 properties across the globe, your Chester travel package can be tailored exactly to suit your budget. With all that extra money, why not include one or more interesting tours and activities? It's an easy way to unlock even more bargains. That holiday you've always dreamed of in Chester is much closer than you thought! ### Does Expedia offer Book Now, Pay Later Chester holidays? Your bank balance shouldn't prevent you from taking a holiday, so Expedia has worked out a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book an incredible getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Check out these flexible payment options: - Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true. - Pay in instalments holidays: If you'd prefer to pay off your getaway across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna. - Low deposit holidays: Pressing the "book now" button is easier with this option. Just put down a small deposit on your booking and then start working on your travel itinerary. ### Where should I stay in Chester? With loads to explore in Chester, we suggest you stay near its attractions. Norma Terris Theatre, Chester Creek Marina and Plattwood Park are some good ones to add to your itinerary. ### What are the top hotels in Chester? [Saybrook Point Resort & Marina](https://www.expedia.co.uk/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) and [Pier Blue Inn Old Saybrook - Essex](https://www.expedia.co.uk/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) are among the most popular hotels in Chester. Why not check out the amenities and facilities at each and then make a decision? ### How far in advance should I book my Chester holiday? Search Expedia to compare international flights as soon as you know your travel dates. You can generally purchase a ticket up to a year prior to departure. If you can't find your preferred air carrier, or you're booking late, fear not. Cheap tickets to Chester sometimes appear a few weeks before the date of departure. ### What does an Expedia Chester travel package include? From hotels and flights to rental cars, Expedia can help you put together a Chester package that's ideal for you. Heading away for a few weeks? Check out a rental car, flight and hotel bundle. If you're taking a short break, a flight and hotel deal may suit you better. Experiences can also be added once you've made your booking. Our packages make it a breeze to save and plan. ### What should I know before booking a Chester travel package? Tailor deals that fit your budget with an Expedia package. Hotels, flights, rental cars — we've got everything you need to plan your getaway. You'll save a packet just for bundling your bookings. Whether you're going on a snow and ski adventure or drinking cocktails on a beach, your ideal getaway is only clicks away. ### Can I choose my airline with a Chester Expedia travel package? Yes, so take your pick! We have access to over 550 airlines around the world, so you can design your Chester getaway according to your style and budget. \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/Chester.d183058.Destination-Travel-Guides nb-NO: https://www.expedia.no/Chester.d183058.Reise id-ID: https://www.expedia.co.id/Chester.d183058.Perjalanan en-US: https://www.expedia.com/Chester.d183058.Destination-Travel-Guides fr-FR: https://www.expedia.fr/Chester.d183058.Reservation-Sejours-Voyages en-TW: https://www.expedia.com.tw/en/Chester.d183058.Destination-Travel-Guides ```